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Interaction of metallopyrazoliumylporphyrins with calf thymus DNA

Identifieur interne : 001564 ( Istex/Corpus ); précédent : 001563; suivant : 001565

Interaction of metallopyrazoliumylporphyrins with calf thymus DNA

Auteurs : Daryono H. Tjahjono ; Shunsuke Mima ; Takehiro Akutsu ; Naoki Yoshioka ; Hidenari Inoue

Source :

RBID : ISTEX:1642D1218149EBED06670529AD5D13DF1D549BD5

Abstract

The interaction of transition metal complexes of cationic porphyrins bearing five membered rings, meso-tetrakis(1,2-dimethylpyrazolium-4-yl)porphyrin (MPzP, M=MnIII, NiII, CuII or ZnII), with calf thymus DNA (ctDNA) has been studied. Metalloporphyrins NiPzP and CuPzP are intercalated into the 5′GC3′ step of ctDNA. MnPzP is bound edge-on at the 5′TA3′ step of the minor groove of ctDNA, while ZnPzP is bound face-on at the 5′TA3′ step of the major groove of ctDNA. The binding constants of the metalloporphyrins to ctDNA range from 1.05×105 to 2.66×106 M−1 and are comparable to those of other reported cationic porphyrins. The binding process of the metallopyrazoliumylporphyrins to ctDNA is endothermic and entropically driven. These results have revealed that the kind of central metal ions of metalloporphyrins influences the binding characteristics of the porphyrin to DNA.

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DOI: 10.1016/S0162-0134(01)00186-6

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ISTEX:1642D1218149EBED06670529AD5D13DF1D549BD5

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<note type="content">Fig. 1: Structure of metallotetrakispyrazoliumylporphyrins, [MPzP]I4.</note>
<note type="content">Fig. 2: Visible, CD and MCD spectra of free (solid line) and ctDNA-bound (dashed line) [MnPzP]I4 in phosphate buffer (pH 6.8, μ=0.2 M) at R (=[porphyrin]/[DNA])=0.02.</note>
<note type="content">Fig. 3: Visible, CD and MCD spectra of free (solid line) and ctDNA-bound (dashed line) [NiPzP]I4 in phosphate buffer (pH 6.8, μ=0.2 M) at R (=[porphyrin]/[DNA])=0.02.</note>
<note type="content">Fig. 4: Visible, CD and MCD spectra of free (solid line) and ctDNA-bound (dashed line) [CuPzP]I4 in phosphate buffer (pH 6.8, μ=0.2 M) at R (=[porphyrin]/[DNA])=0.02.</note>
<note type="content">Fig. 5: Visible, CD and MCD spectra of free (solid line) and ctDNA-bound (dashed line) [ZnPzP]I4 in phosphate buffer (pH 6.8, μ=0.2 M) at R (=[porphyrin]/[DNA])=0.02.</note>
<note type="content">Fig. 6: Plots of the relative viscosity of ctDNA versus R value of [MnPzP]I4 (triangles), [NiPzP]I4 (diamonds), [CuPzP]I4 (squares) and [ZnPzP]I4 (circles) in phosphate buffer (pH 6.8, μ=0.2 M) at 30±1°C.</note>
<note type="content">Fig. 7: Plots of the increase in ctDNA melting temperature (ΔTm) versus R values of [MnPzP]I4 (triangles), [NiPzP]I4 (diamonds), [CuPzP]I4 (squares) and [ZnPzP]I4 (circles) in phosphate buffer (pH 6.8, μ=0.2 M).</note>
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<ce:given-name>Hidenari</ce:given-name>
<ce:surname>Inoue</ce:surname>
</ce:author>
<ce:affiliation>
<ce:textfn>Department of Applied Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan</ce:textfn>
</ce:affiliation>
<ce:correspondence id="CORR1">
<ce:label>*</ce:label>
<ce:text>Corresponding author</ce:text>
</ce:correspondence>
<ce:footnote id="FN1">
<ce:label>1</ce:label>
<ce:note-para>On sabbatical leave from Department of Pharmacy, Bandung Institute of Technology, Jalan Ganesha 10, Bandung 40132, Indonesia.</ce:note-para>
</ce:footnote>
</ce:author-group>
<ce:date-received day="23" month="10" year="2000"></ce:date-received>
<ce:date-revised day="17" month="1" year="2001"></ce:date-revised>
<ce:date-accepted day="22" month="1" year="2001"></ce:date-accepted>
<ce:abstract>
<ce:section-title>Abstract</ce:section-title>
<ce:abstract-sec>
<ce:simple-para>The interaction of transition metal complexes of cationic porphyrins bearing five membered rings,
<ce:italic>meso</ce:italic>
-tetrakis(1,2-dimethylpyrazolium-4-yl)porphyrin (MPzP, M=Mn
<ce:sup>III</ce:sup>
, Ni
<ce:sup>II</ce:sup>
, Cu
<ce:sup>II</ce:sup>
or Zn
<ce:sup>II</ce:sup>
), with calf thymus DNA (ctDNA) has been studied. Metalloporphyrins NiPzP and CuPzP are intercalated into the 5′GC3′ step of ctDNA. MnPzP is bound edge-on at the 5′TA3′ step of the minor groove of ctDNA, while ZnPzP is bound face-on at the 5′TA3′ step of the major groove of ctDNA. The binding constants of the metalloporphyrins to ctDNA range from 1.05×10
<ce:sup>5</ce:sup>
to 2.66×10
<ce:sup>6</ce:sup>
M
<ce:sup>−1</ce:sup>
and are comparable to those of other reported cationic porphyrins. The binding process of the metallopyrazoliumylporphyrins to ctDNA is endothermic and entropically driven. These results have revealed that the kind of central metal ions of metalloporphyrins influences the binding characteristics of the porphyrin to DNA.</ce:simple-para>
</ce:abstract-sec>
</ce:abstract>
<ce:keywords class="keyword">
<ce:section-title>Keywords</ce:section-title>
<ce:keyword>
<ce:text>Cationic pyrazoliumylporphyrin</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Metalloporphyrins</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Calf thymus DNA</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Porphyrin–DNA interaction</ce:text>
</ce:keyword>
<ce:keyword>
<ce:text>Thermodynamic parameters</ce:text>
</ce:keyword>
</ce:keywords>
</head>
</converted-article>
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<title>Interaction of metallopyrazoliumylporphyrins with calf thymus DNA</title>
</titleInfo>
<titleInfo type="alternative" contentType="CDATA">
<title>Interaction of metallopyrazoliumylporphyrins with calf thymus DNA</title>
</titleInfo>
<name type="personal">
<namePart type="given">Daryono H</namePart>
<namePart type="family">Tjahjono</namePart>
<affiliation>Department of Applied Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan</affiliation>
<affiliation>E-mail: c02935@educ.cc.keio.ac.jp</affiliation>
<description>Corresponding author</description>
<description>On sabbatical leave from Department of Pharmacy, Bandung Institute of Technology, Jalan Ganesha 10, Bandung 40132, Indonesia.</description>
<role>
<roleTerm type="text">author</roleTerm>
</role>
</name>
<name type="personal">
<namePart type="given">Shunsuke</namePart>
<namePart type="family">Mima</namePart>
<affiliation>Department of Applied Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan</affiliation>
<role>
<roleTerm type="text">author</roleTerm>
</role>
</name>
<name type="personal">
<namePart type="given">Takehiro</namePart>
<namePart type="family">Akutsu</namePart>
<affiliation>Department of Applied Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan</affiliation>
<role>
<roleTerm type="text">author</roleTerm>
</role>
</name>
<name type="personal">
<namePart type="given">Naoki</namePart>
<namePart type="family">Yoshioka</namePart>
<affiliation>Department of Applied Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan</affiliation>
<role>
<roleTerm type="text">author</roleTerm>
</role>
</name>
<name type="personal">
<namePart type="given">Hidenari</namePart>
<namePart type="family">Inoue</namePart>
<affiliation>Department of Applied Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan</affiliation>
<role>
<roleTerm type="text">author</roleTerm>
</role>
</name>
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<dateIssued encoding="w3cdtf">2001</dateIssued>
<dateModified encoding="w3cdtf">2001-01-17</dateModified>
<copyrightDate encoding="w3cdtf">2001</copyrightDate>
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<abstract lang="en">The interaction of transition metal complexes of cationic porphyrins bearing five membered rings, meso-tetrakis(1,2-dimethylpyrazolium-4-yl)porphyrin (MPzP, M=MnIII, NiII, CuII or ZnII), with calf thymus DNA (ctDNA) has been studied. Metalloporphyrins NiPzP and CuPzP are intercalated into the 5′GC3′ step of ctDNA. MnPzP is bound edge-on at the 5′TA3′ step of the minor groove of ctDNA, while ZnPzP is bound face-on at the 5′TA3′ step of the major groove of ctDNA. The binding constants of the metalloporphyrins to ctDNA range from 1.05×105 to 2.66×106 M−1 and are comparable to those of other reported cationic porphyrins. The binding process of the metallopyrazoliumylporphyrins to ctDNA is endothermic and entropically driven. These results have revealed that the kind of central metal ions of metalloporphyrins influences the binding characteristics of the porphyrin to DNA.</abstract>
<note type="content">Fig. 1: Structure of metallotetrakispyrazoliumylporphyrins, [MPzP]I4.</note>
<note type="content">Fig. 2: Visible, CD and MCD spectra of free (solid line) and ctDNA-bound (dashed line) [MnPzP]I4 in phosphate buffer (pH 6.8, μ=0.2 M) at R (=[porphyrin]/[DNA])=0.02.</note>
<note type="content">Fig. 3: Visible, CD and MCD spectra of free (solid line) and ctDNA-bound (dashed line) [NiPzP]I4 in phosphate buffer (pH 6.8, μ=0.2 M) at R (=[porphyrin]/[DNA])=0.02.</note>
<note type="content">Fig. 4: Visible, CD and MCD spectra of free (solid line) and ctDNA-bound (dashed line) [CuPzP]I4 in phosphate buffer (pH 6.8, μ=0.2 M) at R (=[porphyrin]/[DNA])=0.02.</note>
<note type="content">Fig. 5: Visible, CD and MCD spectra of free (solid line) and ctDNA-bound (dashed line) [ZnPzP]I4 in phosphate buffer (pH 6.8, μ=0.2 M) at R (=[porphyrin]/[DNA])=0.02.</note>
<note type="content">Fig. 6: Plots of the relative viscosity of ctDNA versus R value of [MnPzP]I4 (triangles), [NiPzP]I4 (diamonds), [CuPzP]I4 (squares) and [ZnPzP]I4 (circles) in phosphate buffer (pH 6.8, μ=0.2 M) at 30±1°C.</note>
<note type="content">Fig. 7: Plots of the increase in ctDNA melting temperature (ΔTm) versus R values of [MnPzP]I4 (triangles), [NiPzP]I4 (diamonds), [CuPzP]I4 (squares) and [ZnPzP]I4 (circles) in phosphate buffer (pH 6.8, μ=0.2 M).</note>
<note type="content">Table 1: Thermodynamic parameters of interactions between [MPzP]I4 and ctDNAa</note>
<subject>
<genre>Keywords</genre>
<topic>Cationic pyrazoliumylporphyrin</topic>
<topic>Metalloporphyrins</topic>
<topic>Calf thymus DNA</topic>
<topic>Porphyrin–DNA interaction</topic>
<topic>Thermodynamic parameters</topic>
</subject>
<relatedItem type="host">
<titleInfo>
<title>Journal of Inorganic Biochemistry</title>
</titleInfo>
<titleInfo type="abbreviated">
<title>JIB</title>
</titleInfo>
<genre type="journal">journal</genre>
<originInfo>
<dateIssued encoding="w3cdtf">200106</dateIssued>
</originInfo>
<identifier type="ISSN">0162-0134</identifier>
<identifier type="PII">S0162-0134(00)X0252-8</identifier>
<part>
<date>200106</date>
<detail type="volume">
<number>85</number>
<caption>vol.</caption>
</detail>
<detail type="issue">
<number>2–3</number>
<caption>no.</caption>
</detail>
<extent unit="issue pages">
<start>79</start>
<end>236</end>
</extent>
<extent unit="pages">
<start>219</start>
<end>228</end>
</extent>
</part>
</relatedItem>
<identifier type="istex">1642D1218149EBED06670529AD5D13DF1D549BD5</identifier>
<identifier type="DOI">10.1016/S0162-0134(01)00186-6</identifier>
<identifier type="PII">S0162-0134(01)00186-6</identifier>
<accessCondition type="use and reproduction" contentType="copyright">©2001 Elsevier Science B.V.</accessCondition>
<recordInfo>
<recordContentSource>ELSEVIER</recordContentSource>
<recordOrigin>Elsevier Science B.V., ©2001</recordOrigin>
</recordInfo>
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